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Author: Subject: Tetrameric Acetone Peroxide
cyclonitepyro
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[*] posted on 1-11-2011 at 17:03
Tetrameric Acetone Peroxide


Hello I used to be a member of the E&W forum back ten or eleven years ago with the same username.
Started reading a bit and re hashing fond memories and developed a curiosity about tetrameric AP after reading that pdf. If one had SnCl2 but not the hydrate you could just make the hydrate by evap. a HCl solution, but wouldn't adding the dehydrated SnCl2 into the acetone and H2O2 be the same ions in solution from the water in the H2O2 right? The SnCl2 wont hydrolyse too fast in water will it, not like you can add a SnCl2 in HCl solution to the acetone and H2O2 because then you would have a tetra/tri-meric mix.
Curious also about adding EDTA to the mix for yield improvement but wondering why that is the case and which of the many forms of it they meant in the paper. For example if it was calcium di-sodium EDTA would the calcium or sodium cause any side reactions?
I think standardizing a preparation of this should be established since if viable, should be the only form made.
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AndersHoveland
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[*] posted on 1-11-2011 at 17:29


I am fairly certain that H2O2 would oxidize a solution of SnCl2 into some form of stannic acid (for example H2SnO3).

I do not know what they mean by a "hydrate of SnCl4". Tin tetrachloride is a liquid that reacts with traces of water to form solid metastannic acid.

The Journal of the Chemical Society mentions:
"The evolution of heat in the reduction of hydrogen peroxide by stannous chloride... into stannic oxide"

[Edited on 2-11-2011 by AndersHoveland]
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cyclonitepyro
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[*] posted on 2-11-2011 at 05:00


SnCl4 forms a pentahydrate with a little water. Basically wanting to understand if there is any difference between using either SnCl2 or SnCl4 in dehydrated or hydrated form since there is water in the reaction mix. Thinking these two don't hydrolyse fast enough to worry about or perhaps this is the purpose of adding EDTA to the rxn since acidic conditions prevent hydrolysis.

[Edited on 2-11-2011 by cyclonitepyro]
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Adas
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[*] posted on 2-11-2011 at 09:31


This topic is very interesting to me, but I think it needs some kind of radical initiator or something like that. Or maybe attaching some functional group onto the CH3 group of acetone, which will cause higher polymerisation, and then removing it (just guessing).
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[*] posted on 2-11-2011 at 10:19


I also wonder if somethink like acetamide peroxide can be made. But I haven't found any reference, so probably not. But it is worth a try. But it will probably be very, VERY unstable.
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[*] posted on 2-11-2011 at 12:33


Quote: Originally posted by Adas  
I also wonder if somethink like acetamide peroxide can be made.


I do not think so, but some iminoperacetic acid, HOOC(=NH)CH3 , forms in equilibrium in a mixture of acetamide and hydrogen peroxide.
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[*] posted on 2-11-2011 at 13:47


Okay, and do you know any use of iminoperacetic acid?
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cyclonitepyro
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[*] posted on 8-11-2011 at 06:23


well I'm just going to assume then one could use the dehydrate of SnCl2 just the same as the hydrate. I'm now very curious on what would happen using this catalyst on MEK or better yet a mix of MEK/Acetone. Probably would be better to make the MEKP because everyone knows how to make the desirable dimeric liquid type and then add tetrameric AP to the MEKP. Then add this to DBSP or ETN in some combo for a good cap.
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[*] posted on 8-11-2011 at 11:16


I think you're right. SnCl2 (SnCl4) can be also used as a hydrate. It is not a problem, that it dissociates in water. Even acids do so, and it is no problem in TATP synthesis.

It would be nice to make polymeric AP :D
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[*] posted on 16-9-2018 at 13:28


In reality, SnCl2 catalysed peroxydation also produces TATP. See [8] , Table 2. Influence of catalyst to acetone ratio on the composition
of prepared samples...

Primary Explosives - Robert Matyáš, Jiří Pachman (auth.) , p.275
Jiang [100] has reported a method of preparation of TeATeP using the reaction of acetone with hydrogen peroxide in presence of tin (II and IV) chloride or hydrochloric acid as the catalyst [100]. This method can however be disputed andaccording to our experience, normal TATP is formed [8].

100. Jiang, H., Chu, G., Gong, H., Qiao, Q.: Tin chloride catalysed oxidation of acetone with
hydrogen peroxide to tetrameric acetone peroxide. J. Chem. Res. (S), 288–289 (1999)


8. Matya´sˇ, R., Pachman, J.: Study of TATP: Influence of reaction conditions on product
composition. Propellants Explosives Pyrotechnics 35, 31–37 (2010)

This substance is reported to be tetraacetone tetraperoxide; 3,3,6,6,9,9,12,12-octamethyl-1,2,4,5,7,8,10,11-octaoxacyclododecane (TeATeP)by Schulte-Ladbeck et al. [20], Pena Quevedo et al. [21] or as a structural conformer of TATP by Widmer et al. [22]. We did not analyze this side product further. It was impossible to remove this substance by repeated recrystallization or sublimation.As we have found and published previously [23, 24] it is possible to reduce the amount of this substance by long-termthermal treatment at higher temperatures.

The formation of tetraacetone tetraperoxide by ozonolysis (see reaction above)of tetramethylethene or isobutene has been described by Obinokov et al. [101]. These authors report a melting point of 61–65 C.


101. Obinokov, V.N., Botsman, L.P., Ishmupatov, L.J., Tolstikov, G.A.: Ozonoliz alkenov i izuchenie reakcii polifunkcionalnykh coedinenii. XVIII. Issledovanije novogo ozonoliticheskogo sinteza karbonovykh kislot. Zhurnal organicheskoi khimii 16, 524–537 (1980)


It is worth to mention this patent though "Method for preparing acetone peroxide tetramer" CN102584782A (2012) , which seems to be fake and dangerous to perform as well.


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